Italy: Matera, Otranto & the Puglia Coast

Parco Regionale della Murgia Materana; 2-3.5 miles, easy to moderate and Matera guided walking tour; 2 miles, easy

After enjoying an included breakfast at your hotel your guides will meet you at 8:30 a.m. on the terrace above the lobby of the Dimora Don Ferrante in Monopoli. They’ll be wearing Country Walkers shirts. Please be dressed for walking (hiking shoes are required).

Upon meeting in Monopoli, you travel 75-90 minutes to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was called Lucania. Today, locals still consider themselves—and their deeply traditional cuisine—Lucanian rather than Basilicatan. This morning’s trailhead is in the Parco Regionale della Murgia Materana. This magnificent park fed by the Bradano River and the minor streams of Gravina and Jesce hosts a wide diversity of flora and fauna: its 1,200 botanical species comprise one-sixth of the nation’s and one-third of the region’s in just over 17,000 acres. Foxes, hares, porcupines, and wild boars and cats roam the area as birds of prey like the Lanner falcon, Egyptian vulture, and lesser Kestrel take wing overhead.

Our first day of walking transports you back in time to a region of mystical abandoned caves and hushed ghost villages. The park is home to primitive-looking jazzi—communal settlements where shepherds lived with their livestock well into the 20th century. But what might be considered most fascinating are the spectacular rock-carved cave churches that dot the area and are known as chiese rupestri. (You’ll visit one later this afternoon with a local guide.)

This morning’s trail in the Neolithic village of Murgia Timone leads to a magnificent Belvedere, or lookout. This is where the crucifixion scene was shot in the Passion of the Christ, and it provides a spectacular view of Matera and the adjacent plunging ravine. After time to take in this dramatic vista, retrace your steps to meet up with your minibus and driver for the transfer to lunch, or continue into town by foot, crossing the famed Ponte Tibetano, the Tibetan Bridge, a thrilling board-and-rope span across the Gravina River. Note: this option may not be available for safety reasons. Your guides will inform you in the welcome meeting of the trails open within the park.

Pause for lunch at an ancient oil mill, savoring locally made antipasti such as salami with fennel, Lampascioni (a cousin to garlic), sundried tomatoes, mixed greens, local cheeses (pecorino, caciocavallo, and caprino), and grilled sausage with wild herbs. After lunch, get acquainted with the city of Matera during a walking tour with a local guide. This remarkable city is one of the oldest continuously inhabited cities in the world, a fascinating blend of old and new. As you explore you learn about the lifestyle of the former cave residents, such as the “open door” attitude that extended a welcome to all. Courtyards and a maze of alleyways lead from the cathedral, from where you can enjoy a beautiful view of the Sasso Barisano. This is the sassi (literally, “the Stones”) a dense cluster of yellow-white structures that seem to emerge from the earth. Within this starkly beautiful canvas, you walk among typical dwellings, soaring cathedrals, and cavernous edifices. It’s easy to see how it became a stand-in for ancient Jerusalem in the film The Passion of the Christ.

Continue on foot to your luxury hotel—an albergo diffuso spread out across several cave dwellings carved into the tuff rock, where you settle in and refresh before reuniting with your guides and travel companions for a welcome aperitivo, taking in the sassi’s incomparable architectural profile. Then savor a special seasonal dinner and a glass or two of the native primitivo wine.

Included Meals: Breakfast, Lunch, Dinner

3 miles, easy to moderate, 570-ft. elevation gain and 795-ft. elevation loss

Awaken to a generous breakfast of cheeses and other local delicacies, an assortment of yogurts, cereals, juices, fresh-baked loaves of bread and pastries, fruit, and, of course, cappuccino!

After a brief walk through the maze of alleyways of Matera, you arrive in the town center where you begin a scenic drive to the Dolomiti Lucane—the southern Dolomites. Amidst this otherworldly setting, you stop first in Castelmezzano. Listed as one of Italy’s most beautiful hamlets, it enjoys a dramatic setting, wedged in a cradle-like basin at the foot of soaring, needle-like massifs. Here, you trace an easygoing circuit around this typical medieval village. Magnificent mountain views accompany you throughout this unforgettable walk.

Make your way to the panoramic terrace of our friend and accomplished chef/restaurateur Antonietta. Antonietta embraces fresh, regional ingredients and the local wild harvest of herbs in her preparations, all inspired by her two muses: her mother and her grandmother. Depending on what’s fresh, you might savor homemade cavatelli pasta with crispy-fried peppers (peperoni cruschi) or local cardoncelli mushrooms. No matter what’s in season, your lunch will be a meal to remember—regional dishes served alfresco and accompanied by grandiose mountain views and perhaps a glass of delicious ficotto, or fig wine.

This afternoon, you return to Matera with time to relax at your hotel or visit some of the many cultural attractions. Afterward, enjoy an evening of independent exploring and dining with recommendations from your guides.

Included Meals: Breakfast, Lunch

4 miles, easy

Today you leave the cultural richness of Matera behind and travel to the lush Valle d’Itria in central Puglia. Blanketed with vineyards and olive groves, the valley is dotted with hundreds of trulli, curious stone structures used by Apulian farmers of centuries past. The buildings feature circular, whitewashed walls and cone-shaped roofs; they were originally constructed without mortar so as to make the structures temporary (an ancient tax loophole!). These “beehives” compel close examination—notably, look for the Paleo-Christian good-luck symbols painted on the roofs.

You reach your trailhead near the 11th-century church of Santa Maria di Barsento, a neighboring town of Alberobello. A picturesque walk leads through green pastures, woodland, and along country lanes flanked by stone walls and seemingly endless olive groves and trulli. Soon, you arrive in the village of Alberobello, a UNESCO World Heritage site whose streets are literally packed with trulli. One of these historic beehive buildings has been transformed into an inviting enoteca; you stop by to meet Gino, who offers a wine tasting along with a light lunch of traditional Apulian snacks.

Following lunch, there is time for you to explore this fairy-tale town on your own; your guides will orient you to the town’s layout. Perhaps head to Piazza del Popolo, or People’s Square, to seek out the town’s hand-woven linens, filet lace, and ceramics at the charming artisanal boutiques. You might also visit the church of St. Anthony, which shares the trulli architectural aesthetic. Or, pop into Pasticceria Martinucci for a delicious gelato.

After, you journey to the “white city” of Ostuni, so nicknamed for its whitewashed buildings. After settling in to your hotel, step out with your guides for a special experience and an introduction to this hilltop town overlooking the Adriatic.  Admire its largest buildings including the dramatic 15th-century Ostuni Cathedral and the Bishop’s Palace. Other palazzi stand as legacies to an array of aristocratic families that have made their mark on the town. Afterward, pause for an aperitivo or to shop for some locally crafted ceramics as mementos. For dinner on your own, perhaps dine at one of their favorite osterias along the route. Alternatively, enjoy a relaxing late afternoon at the hotel’s spa, followed by dinner at the hotel’s outstanding bistrot.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take some time to linger over a leisurely breakfast. Bidding farewell to Ostuni, you travel south toward the medieval port of Otranto, your home for the next three nights. En route, stop at an estate near Uggiano la Chiesa in a peaceful oasis blanketed by olive groves and Mediterranean macchia, or scrub. Visit the award-winning passion project of sisters Giulia and Lucia Starace. Here, a team of dedicated weavers works to keep textile arts alive in the 21st century by educating local children about traditional crafts and responsible culture. On arrival, you walk past bushes of myrtle, holm oaks, wild orchids and one of the oldest beehives in the region. Enjoy a demonstration at the weaving cooperative, recently tapped to contribute to the cruise collection of Parisian fashion house Dior. After, delight in a delicious lunch on the grounds of this special property.

Depart on foot for an easy afternoon walk into the Bronze Age. Your destination is Italy’s megalithic garden in and around neighboring Giurdignano. Home to more than 25 standing-stone menhirs and dolmen, the site provides remarkable insight into an often forgotten past. Continue your exploration with a visit to an underground olive mill, built in the 16th century, and the 8th-century crypt of San Salvatore, adorned with remarkably preserved 13th-century frescoes.

Your walk culminates at a beautiful whitewashed masseria just outside Otranto, and your home for the next three nights. Enjoy an aperitivo upon arrival, accompanied by typical Salentino snacks. Dinner is on your own this evening; a shuttle is provided into town or you may opt to dine in the masseria’s wonderful restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you travel to Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a scenic location on the Strait of Otranto, which connects the Adriatic and Ionian seas. Greeks, Romans, Byzantines, Normans, and Aragonese have all called this port their own and left their marks on this remarkable city.

This morning’s walking route follows the rocky shores of the Adriatic past rugged coves and caves. Along these coastal cliffs, your progress is marked by the region’s aromatic Mediterranean macchia shrubs and ancient watchtowers—evidence of the defenses erected against Turkish invasions. The stark rocky landscape along the sparkling sea delivers you to a fascinating abandoned bauxite quarry. The stone mined here was once ferried as far away as Venice for the construction of that once-great republic. Today, the quarry resembles a lake in a basin of deep-red walls—hence its local name, Red Lake.

You continue your walk towards the whitewashed Punta Palascia lighthouse, arriving at a family-run agriturismo, where you are welcomed in for a cheesemaking demonstration by a local producer and a light lunch featuring local products—savor antipasti salentini including typical cheeses and homemade bread.

After, continue on foot or by minibus to Porto Badisco, a charming bay whose clear turquoise waters and white-sand floor invite you for a swim. Virgil famously claimed that this sheltered beach was the site of Aeneas’s first landing after he escaped from Troy.

Once you return to the masseria, there’ll be time to relax poolside or treat yourself to a massage before dinner at a nearby winery. This is a truly local experience, and sure to be a highlight of your adventure. After a stroll through the vineyards, with a welcome glass of wine in hand, sit down for a meal that emphasizes the regional specialties. It’s all complemented by a selection of their wines, perhaps a rosé made of the local negroamaro as well as the deep-red native primitivo.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and optional 3 miles, easy

On today’s walk, you trace routes of historical and environmental importance through the Regional Natural Coastal Park of Costa Otranto Santa Maria di Leuca Bosco di Tricase. After breakfast, journey to Marina di Novaglie for the start of your uniquely rewarding day. As you begin, you follow a rocky coastal trail along the sea, passing the typical Salento pajare along the way. These dry-stone structures, like the trulli of Alberobello, might have had their origins as temporary shelters, agricultural storehouses, or dwellings for farm workers.

Your morning destination is Ponte Ciolo, or Ciolo’s Bridge. The town may have been named for the Salentino dialect ciole, or magpies, which are ubiquitous in the region. Several botanical rarities—from Mediterranean onion species to ferns, flowers, and several types of orchids—call this scenic place home, too. Ponte Ciolo gracefully straddles a narrow coastal inlet that has carved out numerous sea caves. Fossils, including those of rhinoceros, and ceramics dating to the Neolithic and the Paleolithic periods, have been found in these remarkable grottoes. Time permitting, you have the option to venture down into the Grotta delle Cipolliane. Though the excursion is not for everyone—it requires negotiating rocks and numerous steps—your effort will be rewarded by being able to dip your toes in the sea. During your time in this scenic enclave, enjoy a break to relax and swim if you wish. There’ll be time for a coffee or drink before continuing on to Santa Maria di Leuca by minibus.

Santa Maria di Leuca is the spot where the Adriatic and Ionian seas swirl together as well as the southernmost point of the Via Francigena. This ancient pilgrim’s route (it translates into “the road from France”) stretches from Canterbury, England to Rome, then continues to Puglia, where pilgrims once continued to the Holy Land by boat. Centuries of other visitors—including traders, pirates, and invaders—have also shaped the history and culture of Capo di Leuca. Upon arrival, you can visit an important religious sanctuary above the town’s harbor—the Basilica de Finibus Terrae, which translates to “basilica at the end of the earth,” an apt term for this seaside outpost at the end of the empire. Your guides will also offer an optional walk along the seaside promenade, pointing out restaurants for lunch on your own. Afterward, return to your masseria, where there’ll be time to relax before the evening meal.

For your final dinner together, you are welcomed at the hotel’s alfresco restaurant with a glass of sparkling prosecco. Settle in for a memorable meal that features the seasonal bounty of the region. You may savor a creamy troccoli: pasta with cuttlefish and black chickpea cream, or risotto with violet shrimp of Gallipoli, pistachios, and pesto, paired with a glass or two of local vino! It’s the ideal way to toast your discovery of the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you stop in the port of Otranto for an hour-long walking tour with your guide. This stunning coastal city boasts a spectacular waterfront and a fascinating medieval past. The city’s highlight is Otranto Cathedral’s enormous, 8,611-square-foot floor mosaic representing the Tree of Life, created by a monk in 1163. Afterward, enjoy free time to explore local craft studios selling clay whistles, baskets, hand-dyed fabric, and ceramics.

Journey finally to Lecce, the “Florence of the South.” Bid farewell to your Country Walkers guides midday at the Patria Palace Hotel, and the remainder of the day is yours to uncover the wonders of this remarkable city. Lunch and dinner are on your own. We provide detailed city information to help you plan your stay.

Included Meals: Breakfast

Parco Regionale della Murgia Materana; 2-3.5 miles, easy to moderate and Matera guided walking tour; 2 miles, easy

After enjoying an included breakfast at your hotel your guides will meet you at 8:30 a.m. in the lobby of the Grande Albergo delle Nazioni in Bari. They’ll be wearing Country Walkers shirts. Please be dressed for walking (hiking shoes are required).

Upon meeting in Bari, you travel approximately 60 minutes to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was called Lucania. Today, locals still consider themselves—and their deeply traditional cuisine—Lucanian rather than Basilicatan. This morning’s trailhead is in the Parco Regionale della Murgia Materana. This magnificent park fed by the Bradano River and the minor streams of Gravina and Jesce hosts a wide diversity of flora and fauna: its 1,200 botanical species comprise one-sixth of the nation’s and one-third of the region’s in just over 17,000 acres. Foxes, hares, porcupines, and wild boars and cats roam the area as birds of prey like the Lanner falcon, Egyptian vulture, and lesser Kestrel take wing overhead.

Our first day of walking transports you back in time to a region of mystical abandoned caves and hushed ghost villages. The park is home to primitive-looking jazzi—communal settlements where shepherds lived with their livestock well into the 20th century. But what might be considered most fascinating are the spectacular rock-carved cave churches that dot the area and are known as chiese rupestri. (You’ll visit one later this afternoon with a local guide.)

This morning’s trail in the Neolithic village of Murgia Timone leads to a magnificent Belvedere, or lookout. This is where the crucifixion scene was shot in the Passion of the Christ, and it provides a spectacular view of Matera and the adjacent plunging ravine. After time to take in this dramatic vista, retrace your steps to meet up with your minibus and driver for the transfer to lunch, or continue into town by foot, crossing the famed Ponte Tibetano, the Tibetan Bridge, a thrilling board-and-rope span across the Gravina River. Note: this option may not be available for safety reasons. Your guides will inform you in the welcome meeting of the trails open within the park.

Pause for lunch at an ancient oil mill, savoring locally made antipasti such as salami with fennel, Lampascioni (a cousin to garlic), sundried tomatoes, mixed greens, local cheeses (pecorino, caciocavallo, and caprino), and grilled sausage with wild herbs. After lunch, get acquainted with the city of Matera during a walking tour with a local guide. This remarkable city is one of the oldest continuously inhabited cities in the world, a fascinating blend of old and new. As you explore you learn about the lifestyle of the former cave residents, such as the “open door” attitude that extended a welcome to all. Courtyards and a maze of alleyways lead from the cathedral, from where you can enjoy a beautiful view of the Sasso Barisano. This is the sassi (literally, “the Stones”) a dense cluster of yellow-white structures that seem to emerge from the earth. Within this starkly beautiful canvas, you walk among typical dwellings, soaring cathedrals, and cavernous edifices. It’s easy to see how it became a stand-in for ancient Jerusalem in the film The Passion of the Christ.

Continue on foot to your luxury hotel—an albergo diffuso spread out across several cave dwellings carved into the tuff rock, where you settle in and refresh before reuniting with your guides and travel companions for a welcome aperitivo, taking in the sassi’s incomparable architectural profile. Then savor a special seasonal dinner and a glass or two of the native primitivo wine.

Included Meals: Breakfast, Lunch, Dinner

3 miles, easy to moderate, 570-ft. elevation gain and 795-ft. elevation loss

Awaken to a generous breakfast of cheeses and other local delicacies, an assortment of yogurts, cereals, juices, fresh-baked loaves of bread and pastries, fruit, and, of course, cappuccino!

After a brief walk through the maze of alleyways of Matera, you arrive in the town center where you begin a scenic drive to the Dolomiti Lucane—the southern Dolomites. Amidst this otherworldly setting, you stop first in Castelmezzano. Listed as one of Italy’s most beautiful hamlets, it enjoys a dramatic setting, wedged in a cradle-like basin at the foot of soaring, needle-like massifs. Here, you trace an easygoing circuit around this typical medieval village. Magnificent mountain views accompany you throughout this unforgettable walk.

Make your way to the panoramic terrace of our friend and accomplished chef/restaurateur Antonietta. Antonietta embraces fresh, regional ingredients and the local wild harvest of herbs in her preparations, all inspired by her two muses: her mother and her grandmother. Depending on what’s fresh, you might savor homemade cavatelli pasta with crispy-fried peppers (peperoni cruschi) or local cardoncelli mushrooms. No matter what’s in season, your lunch will be a meal to remember—regional dishes served alfresco and accompanied by grandiose mountain views and perhaps a glass of delicious ficotto, or fig wine.

This afternoon, you return to Matera with time to relax at your hotel or visit some of the many cultural attractions. Afterward, enjoy an evening of independent exploring and dining with recommendations from your guides.

Included Meals: Breakfast, Lunch

4 miles, easy

Today you leave the cultural richness of Matera behind and travel to the lush Valle d’Itria in central Puglia. Blanketed with vineyards and olive groves, the valley is dotted with hundreds of trulli, curious stone structures used by Apulian farmers of centuries past. The buildings feature circular, whitewashed walls and cone-shaped roofs; they were originally constructed without mortar so as to make the structures temporary (an ancient tax loophole!). These “beehives” compel close examination—notably, look for the Paleo-Christian good-luck symbols painted on the roofs.

You reach your trailhead near the 11th-century church of Santa Maria di Barsento, a neighboring town of Alberobello. A picturesque walk leads through green pastures, woodland, and along country lanes flanked by stone walls and seemingly endless olive groves and trulli. Soon, you arrive in the village of Alberobello, a UNESCO World Heritage site whose streets are literally packed with trulli. One of these historic beehive buildings has been transformed into an inviting enoteca; you stop by to meet Gino, who offers a wine tasting along with a light lunch of traditional Apulian snacks.

Following lunch, there is time for you to explore this fairy-tale town on your own; your guides will orient you to the town’s layout. Perhaps head to Piazza del Popolo, or People’s Square, to seek out the town’s hand-woven linens, filet lace, and ceramics at the charming artisanal boutiques. You might also visit the church of St. Anthony, which shares the trulli architectural aesthetic. Or, pop into Pasticceria Martinucci for a delicious gelato.

After, you journey to the “white city” of Ostuni, so nicknamed for its whitewashed buildings. After settling into your hotel, step out with your guides for a special experience and an introduction to this hilltop town overlooking the Adriatic.  Admire its largest buildings including the dramatic 15th-century Ostuni Cathedral and the Bishop’s Palace. Other palazzi stand as legacies to an array of aristocratic families that have made their mark on the town. Afterward, pause for an aperitivo or to shop for some locally crafted ceramics as mementos. For dinner on your own, perhaps dine at one of their favorite osterias along the route. Alternatively, enjoy a relaxing late afternoon at the hotel’s spa, followed by dinner at the hotel’s outstanding bistrot.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take some time to linger over a leisurely breakfast. Bidding farewell to Ostuni, you travel south toward the medieval port of Otranto, your home for the next three nights. En route, stop at an estate near Uggiano la Chiesa in a peaceful oasis blanketed by olive groves and Mediterranean macchia, or scrub. Visit the award-winning passion project of sisters Giulia and Lucia Starace. Here, a team of dedicated weavers works to keep textile arts alive in the 21st century by educating local children about traditional crafts and responsible culture. On arrival, you walk past bushes of myrtle, holm oaks, wild orchids, and one of the oldest beehives in the region. Enjoy a demonstration at the weaving cooperative, recently tapped to contribute to the cruise collection of Parisian fashion house Dior. After, delight in a delicious lunch on the grounds of this special property.

Depart on foot for an easy afternoon walk into the Bronze Age. Your destination is Italy’s megalithic garden in and around neighboring Giurdignano. Home to more than 25 standing-stone menhirs and dolmen, the site provides remarkable insight into an often-forgotten past. Continue your exploration with a visit to an underground olive mill, built in the 16th century, and the 8th-century crypt of San Salvatore, adorned with remarkably preserved 13th-century frescoes.

Your walk culminates at a beautiful whitewashed masseria just outside Otranto, and your home for the next three nights. Enjoy an aperitivo upon arrival, accompanied by typical Salentino snacks. Dinner is on your own this evening; a shuttle is provided into town or you may opt to dine in the masseria’s wonderful restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you travel to Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a scenic location on the Strait of Otranto, which connects the Adriatic and Ionian seas. Greeks, Romans, Byzantines, Normans, and Aragonese have all called this port their own and left their marks on this remarkable city.

This morning’s walking route follows the rocky shores of the Adriatic past rugged coves and caves. Along these coastal cliffs, your progress is marked by the region’s aromatic Mediterranean macchia shrubs and ancient watchtowers—evidence of the defenses erected against Turkish invasions. The stark rocky landscape along the sparkling sea delivers you to a fascinating abandoned bauxite quarry. The stone mined here was once ferried as far away as Venice for the construction of that once-great republic. Today, the quarry resembles a lake in a basin of deep-red walls—hence its local name, Red Lake.

You continue your walk towards the whitewashed Punta Palascia lighthouse, arriving at a family-run agriturismo, where you are welcomed in for a cheesemaking demonstration by a local producer and a light lunch featuring local products—savor antipasti salentini including typical cheeses and homemade bread.

After, continue on foot or by minibus to Porto Badisco, a charming bay whose clear turquoise waters and white-sand floor invite you for a swim. Virgil famously claimed that this sheltered beach was the site of Aeneas’s first landing after he escaped from Troy.

Once you return to the masseria, there’ll be time to relax poolside or treat yourself to a massage before dinner at a nearby winery. This is a truly local experience, and sure to be a highlight of your adventure. After a stroll through the vineyards, with a welcome glass of wine in hand, sit down for a meal that emphasizes the regional specialties. It’s all complemented by a selection of their wines, perhaps a rosé made of the local negroamaro as well as the deep-red native primitivo.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and optional 3 miles, easy

On today’s walk, you trace routes of historical and environmental importance through the Regional Natural Coastal Park of Costa Otranto Santa Maria di Leuca Bosco di Tricase. After breakfast, journey to Marina di Novaglie for the start of your uniquely rewarding day. As you begin, you follow a rocky coastal trail along the sea, passing the typical Salento pajare along the way. These dry-stone structures, like the trulli of Alberobello, might have had their origins as temporary shelters, agricultural storehouses, or dwellings for farm workers.

Your morning destination is Ponte Ciolo, or Ciolo’s Bridge. The town may have been named for the Salentino dialect ciole, or magpies, which are ubiquitous in the region. Several botanical rarities—from Mediterranean onion species to ferns, flowers, and several types of orchids—call this scenic place home, too. Ponte Ciolo gracefully straddles a narrow coastal inlet that has carved out numerous sea caves. Fossils, including those of rhinoceros, and ceramics dating to the Neolithic and the Paleolithic periods, have been found in these remarkable grottoes. Time permitting, you have the option to venture down into the Grotta delle Cipolliane. Though the excursion is not for everyone—it requires negotiating rocks and numerous steps—your effort will be rewarded by being able to dip your toes in the sea. During your time in this scenic enclave, enjoy a break to relax and swim if you wish. There’ll be time for a coffee or drink before continuing on to Santa Maria di Leuca by minibus.

Santa Maria di Leuca is the spot where the Adriatic and Ionian seas swirl together as well as the southernmost point of the Via Francigena. This ancient pilgrim’s route (it translates into “the road from France”) stretches from Canterbury, England to Rome, then continues to Puglia, where pilgrims once continued to the Holy Land by boat. Centuries of other visitors—including traders, pirates, and invaders—have also shaped the history and culture of Capo di Leuca. Upon arrival, you can visit an important religious sanctuary above the town’s harbor—the Basilica de Finibus Terrae, which translates to “basilica at the end of the earth,” an apt term for this seaside outpost at the end of the empire. Your guides will also offer an optional walk along the seaside promenade, pointing out restaurants for lunch on your own. Afterward, return to your masseria, where there’ll be time to relax before the evening meal.

For your final dinner together, you are welcomed at the hotel’s alfresco restaurant with a glass of sparkling prosecco. Settle in for a memorable meal that features the seasonal bounty of the region. You may savor a creamy troccoli: pasta with cuttlefish and black chickpea cream, or risotto with violet shrimp of Gallipoli, pistachios, and pesto, paired with a glass or two of local vino! It’s the ideal way to toast your discovery of the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you stop in the port of Otranto for an hour-long walking tour with your guide. This stunning coastal city boasts a spectacular waterfront and a fascinating medieval past. The city’s highlight is Otranto Cathedral’s enormous, 8,611-square-foot floor mosaic representing the Tree of Life, created by a monk in 1163. Afterward, enjoy free time to explore local craft studios selling clay whistles, baskets, hand-dyed fabric, and ceramics.

Journey finally to Lecce, the “Florence of the South.” Bid farewell to your Country Walkers guides midday at the Patria Palace Hotel, and the remainder of the day is yours to uncover the wonders of this remarkable city. Lunch and dinner are on your own. We provide detailed city information to help you plan your stay.

Included Meals: Breakfast

Parco Regionale della Murgia Materana; 2-3.5 miles, easy to moderate and Matera guided walking tour; 2 miles, easy

Your guides will meet you at 8:30 a.m. (after breakfast on your own) on the terrace above the lobby of Dimora Don Ferrante (Via S.Vito, 27, Monopoli, Italy, Tel +39 080 742 521). They’ll be wearing Country Walkers shirts. Please be dressed for walking (hiking shoes required).

Upon meeting in Monopoli, you travel 75-90 minutes to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was called Lucania. Today, locals still consider themselves—and their deeply traditional cuisine—Lucanian rather than Basilicatan. This morning’s trailhead is in the Parco Regionale della Murgia Materana. This magnificent park fed by the Bradano River and the minor streams of Gravina and Jesce hosts a wide diversity of flora and fauna: its 1,200 botanical species comprise one-sixth of the nation’s and one-third of the region’s in just over 17,000 acres. Foxes, hares, porcupines, and wild boars and cats roam the area as birds of prey like the Lanner falcon, Egyptian vulture, and lesser Kestrel take wing overhead.

Our first day of walking transports you back in time to a region of mystical abandoned caves and hushed ghost villages. The park is home to primitive-looking jazzi—communal settlements where shepherds lived with their livestock well into the 20th century. But what might be considered most fascinating are the spectacular rock-carved cave churches that dot the area and are known as chiese rupestri. (You’ll visit one later this afternoon with a local guide.)

This morning’s trail in the Neolithic village of Murgia Timone leads to a magnificent Belvedere, or lookout. This is where the crucifixion scene was shot in the Passion of the Christ, and it provides a spectacular view of Matera and the adjacent plunging ravine. After time to take in this dramatic vista, retrace your steps to meet up with your minibus and driver for the transfer to lunch, or continue into town by foot, crossing the famed Ponte Tibetano, the Tibetan Bridge, a thrilling board-and-rope span across the Gravina River. Note: this option may not be available for safety reasons. Your guides will inform you in the welcome meeting of the trails open within the park.

Pause for lunch at an ancient oil mill, savoring locally made antipasti such as salami with fennel, Lampascioni (a cousin to garlic), sundried tomatoes, mixed greens, local cheeses (pecorino, caciocavallo, and caprino), and grilled sausage with wild herbs. Morning. After lunch, get acquainted with the city of Matera during a walking tour with a local guide. This remarkable city is one of the oldest continuously inhabited cities in the world, a fascinating blend of old and new. As you explore you learn about the lifestyle of the former cave residents, such as the “open door” attitude that extended a welcome to all. Courtyards and a maze of alleyways lead from the cathedral, from where you can enjoy a beautiful view of the Sasso Barisano. This is the sassi (literally, “the Stones”) a dense cluster of yellow-white structures that seem to emerge from the earth. Within this starkly beautiful canvas, you walk among typical dwellings, soaring cathedrals, and cavernous edifices. It’s easy to see how it became a stand-in for ancient Jerusalem in the film The Passion of the Christ.

Continue on foot to your luxury hotel—an albergo diffuso spread out across several cave dwellings carved into the tuff rock. Settle in and refresh before reuniting with your guides and travel companions for a welcome aperitivo, taking in the sassi’s incomparable architectural profile. Then savor a special seasonal dinner and a glass or two of the native primitivo wine.

Included Meals: Lunch, Dinner

3 miles, easy to moderate, 570-ft. elevation gain and 795-ft. elevation loss

Awaken to a generous breakfast of cheeses and other local delicacies, an assortment of yogurts, cereals, juices, fresh-baked loaves of bread and pastries, fruit, and, of course, cappuccino!

After a brief walk through the maze of alleyways of Matera, you arrive in the town center where you begin a scenic drive to the Dolomiti Lucane—the southern Dolomites. Amidst this otherworldly setting, you stop first in Castelmezzano. Listed as one of Italy’s most beautiful hamlets, it enjoys a dramatic setting, wedged in a cradle-like basin at the foot of soaring, needle-like massifs. Here, you trace an easygoing circuit around this typical medieval village. Magnificent mountain views accompany you throughout this unforgettable walk.

Make your way to the panoramic terrace of our friend and accomplished chef/restaurateur Antonietta. Antonietta embraces fresh, regional ingredients and the local wild harvest of herbs in her preparations, all inspired by her two muses: her mother and her grandmother. Depending on what’s fresh, you might savor homemade cavatelli pasta with crispy-fried peppers (peperoni cruschi) or local cardoncelli mushrooms. No matter what’s in season, your lunch will be a meal to remember—regional dishes served alfresco and accompanied by grandiose mountain views and perhaps a glass of delicious ficotto, or fig wine.

This afternoon, you return to Matera with time to relax at your hotel or visit some of the many cultural attractions. Afterward, enjoy an evening of independent exploring and dining with recommendations from your guides.

Included Meals: Breakfast, Lunch

4 miles, easy

Today you leave the cultural richness of Matera behind and travel to the lush Valle d’Itria in central Puglia. Blanketed with vineyards and olive groves, the valley is dotted with hundreds of trulli, curious stone structures used by Apulian farmers of centuries past. The buildings feature circular, whitewashed walls and cone-shaped roofs; they were originally constructed without mortar so as to make the structures temporary (an ancient tax loophole!). These “beehives” compel close examination—notably, look for the Paleo-Christian good-luck symbols painted on the roofs.

You reach your trailhead near the 11th-century church of Santa Maria di Barsento, a neighboring town of Alberobello. A picturesque walk leads through green pastures, woodland, and along country lanes flanked by stone walls and seemingly endless olive groves and trulli. Soon, you arrive in the village of Alberobello, a UNESCO World Heritage site whose streets are literally packed with trulli. One of these historic beehive buildings has been transformed into an inviting enoteca; you stop by to meet Gino, who offers a wine tasting along with a light lunch of traditional Apulian snacks.

Following lunch, there is time for you to explore this fairy-tale town on your own; your guides will orient you to the town’s layout. Perhaps head to Piazza del Popolo, or People’s Square, to seek out the town’s hand-woven linens, filet lace, and ceramics at the charming artisanal boutiques. You might also visit the church of St. Anthony, which shares the trulli architectural aesthetic. Or, pop into Pasticceria Martinucci for a delicious gelato.

After, you journey to the “white city” of Ostuni, so nicknamed for its whitewashed buildings. After settling in to your hotel, step out with your guides for a special experience and an introduction to this hilltop town overlooking the Adriatic.  Admire its largest buildings including the dramatic 15th-century Ostuni Cathedral and the Bishop’s Palace. Other palazzi stand as legacies to an array of aristocratic families that have made their mark on the town. Afterward, pause for an aperitivo or to shop for some locally crafted ceramics as mementos. For dinner on your own, perhaps dine at one of their favorite osterias along the route. Alternatively, enjoy a relaxing late afternoon at the hotel’s spa, followed by dinner at the hotel’s outstanding bistrot.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take some time to linger over a leisurely breakfast. Bidding farewell to Ostuni, you travel south toward the medieval port of Otranto, your home for the next three nights. En route, stop at an estate near Uggiano la Chiesa in a peaceful oasis blanketed by olive groves and Mediterranean macchia, or scrub. Visit the award-winning passion project of sisters Giulia and Lucia Starace. Here, a team of dedicated weavers works to keep textile arts alive in the 21st century by educating local children about traditional crafts and responsible culture. On arrival, you walk past bushes of myrtle, holm oaks, wild orchids and one of the oldest beehives in the region. Enjoy a demonstration at the weaving cooperative, recently tapped to contribute to the cruise collection of Parisian fashion house Dior. After, delight in a delicious lunch on the grounds of this special property.

Depart on foot for an easy afternoon walk into the Bronze Age. Your destination is Italy’s megalithic garden in and around neighboring Giurdignano. Home to more than 25 standing-stone menhirs and dolmen, the site provides remarkable insight into an often forgotten past. Continue your exploration with a visit to an underground olive mill, built in the 16th century, and the 8th-century crypt of San Salvatore, adorned with remarkably preserved 13th-century frescoes.

Your walk culminates at a beautiful whitewashed masseria just outside Otranto, and your home for the next three nights. Enjoy an aperitivo upon arrival, accompanied by typical Salentino snacks. Dinner is on your own this evening; a shuttle is provided into town or you may opt to dine in the masseria’s wonderful restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you travel to Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a scenic location on the Strait of Otranto, which connects the Adriatic and Ionian seas. Greeks, Romans, Byzantines, Normans, and Aragonese have all called this port their own and left their marks on this remarkable city.

This morning’s walking route follows the rocky shores of the Adriatic past rugged coves and caves. Along these coastal cliffs, your progress is marked by the region’s aromatic Mediterranean macchia shrubs and ancient watchtowers—evidence of the defenses erected against Turkish invasions. The stark rocky landscape along the sparkling sea delivers you to a fascinating abandoned bauxite quarry. The stone mined here was once ferried as far away as Venice for the construction of that once-great republic. Today, the quarry resembles a lake in a basin of deep-red walls—hence its local name, Red Lake.

You continue your walk towards the whitewashed Punta Palascia lighthouse, arriving at a family-run agriturismo, where you are welcomed in for a cheesemaking demonstration by a local producer and a light lunch featuring local products—savor antipasti salentini including typical cheeses and homemade bread.

After, continue on foot or by minibus to Porto Badisco, a charming bay whose clear turquoise waters and white-sand floor invite you for a swim. Virgil famously claimed that this sheltered beach was the site of Aeneas’s first landing after he escaped from Troy.

Once you return to the masseria, there’ll be time to relax poolside or treat yourself to a massage before dinner at a nearby winery. This is a truly local experience, and sure to be a highlight of your adventure. After a stroll through the vineyards, with a welcome glass of wine in hand, sit down for a meal that emphasizes the regional specialties. It’s all complemented by a selection of their wines, perhaps a rosé made of the local negroamaro as well as the deep-red native primitivo.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and optional 3 miles, easy

On today’s walk, you trace routes of historical and environmental importance through the Regional Natural Coastal Park of Costa Otranto Santa Maria di Leuca Bosco di Tricase. After breakfast, journey to Marina di Novaglie for the start of your uniquely rewarding day. As you begin, you follow a rocky coastal trail along the sea, passing the typical Salento pajare along the way. These dry-stone structures, like the trulli of Alberobello, might have had their origins as temporary shelters, agricultural storehouses, or dwellings for farm workers.

Your morning destination is Ponte Ciolo, or Ciolo’s Bridge. The town may have been named for the Salentino dialect ciole, or magpies, which are ubiquitous in the region. Several botanical rarities—from Mediterranean onion species to ferns, flowers, and several types of orchids—call this scenic place home, too. Ponte Ciolo gracefully straddles a narrow coastal inlet that has carved out numerous sea caves. Fossils, including those of rhinoceros, and ceramics dating to the Neolithic and the Paleolithic periods, have been found in these remarkable grottoes. Time permitting, you have the option to venture down into the Grotta delle Cipolliane. Though the excursion is not for everyone—it requires negotiating rocks and numerous steps—your effort will be rewarded by being able to dip your toes in the sea. During your time in this scenic enclave, enjoy a break to relax and swim if you wish. There’ll be time for a coffee or drink before continuing on to Santa Maria di Leuca by minibus.

Santa Maria di Leuca is the spot where the Adriatic and Ionian seas swirl together as well as the southernmost point of the Via Francigena. This ancient pilgrim’s route (it translates into “the road from France”) stretches from Canterbury, England to Rome, then continues to Puglia, where pilgrims once continued to the Holy Land by boat. Centuries of other visitors—including traders, pirates, and invaders—have also shaped the history and culture of Capo di Leuca. Upon arrival, you can visit an important religious sanctuary above the town’s harbor—the Basilica de Finibus Terrae, which translates to “basilica at the end of the earth,” an apt term for this seaside outpost at the end of the empire. Your guides will also offer an optional walk along the seaside promenade, pointing out restaurants for lunch on your own. Afterward, return to your masseria, where there’ll be time to relax before the evening meal.

For your final dinner together, you are welcomed at the hotel’s alfresco restaurant with a glass of sparkling prosecco. Settle in for a memorable meal that features the seasonal bounty of the region. You may savor a creamy troccoli: pasta with cuttlefish and black chickpea cream, or risotto with violet shrimp of Gallipoli, pistachios, and pesto, paired with a glass or two of local vino! It’s the ideal way to toast your discovery of the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you stop in the port of Otranto for an hour-long walking tour with your guide. This stunning coastal city boasts a spectacular waterfront and a fascinating medieval past. The city’s highlight is Otranto Cathedral’s enormous, 8,611-square-foot floor mosaic representing the Tree of Life, created by a monk in 1163. Afterward, enjoy free time to explore local craft studios selling clay whistles, baskets, hand-dyed fabric, and ceramics.

Lastly, you will journey to Lecce, the “Florence of the South,” where you tour concludes. Bid farewell to your Country Walkers guides at the Patria Palace Hotel by 12:30 p.m.

Included Meals: Breakfast

Parco Regionale della Murgia Materana; 2-3.5 miles, easy to moderate and Matera guided walking tour; 2 miles, easy

Your guides will meet you at 8:30 a.m. (after breakfast on your own) on the terrace above the lobby of Grande Albergo delle Nazioni. They’ll be wearing Country Walkers shirts. Please be dressed for walking (hiking shoes are required).

Upon meeting in Bari, you travel to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was called Lucania. Today, locals still consider themselves—and their deeply traditional cuisine—Lucanian rather than Basilicatan. This morning’s trailhead is in the Parco Regionale della Murgia Materana. This magnificent park fed by the Bradano River and the minor streams of Gravina and Jesce hosts a wide diversity of flora and fauna: its 1,200 botanical species comprise one-sixth of the nation’s and one-third of the region’s in just over 17,000 acres. Foxes, hares, porcupines, and wild boars and cats roam the area as birds of prey like the Lanner falcon, Egyptian vulture, and lesser Kestrel take wing overhead.

Our first day of walking transports you back in time to a region of mystical abandoned caves and hushed ghost villages. The park is home to primitive-looking jazzi—communal settlements where shepherds lived with their livestock well into the 20th century. But what might be considered most fascinating are the spectacular rock-carved cave churches that dot the area and are known as chiese rupestri. (You’ll visit one later this afternoon with a local guide.)

This morning’s trail in the Neolithic village of Murgia Timone leads to a magnificent Belvedere, or lookout. This is where the crucifixion scene was shot in the Passion of the Christ, and it provides a spectacular view of Matera and the adjacent plunging ravine. After time to take in this dramatic vista, retrace your steps to meet up with your minibus and driver for the transfer to lunch, or continue into town by foot, crossing the famed Ponte Tibetano, the Tibetan Bridge, a thrilling board-and-rope span across the Gravina River. Note: this option may not be available for safety reasons. Your guides will inform you in the welcome meeting of the trails open within the park.

Pause for lunch at an ancient oil mill, savoring locally made antipasti such as salami with fennel, Lampascioni (a cousin to garlic), sundried tomatoes, mixed greens, local cheeses (pecorino, caciocavallo, and caprino), and grilled sausage with wild herbs. Morning. After lunch, get acquainted with the city of Matera during a walking tour with a local guide. This remarkable city is one of the oldest continuously inhabited cities in the world, a fascinating blend of old and new. As you explore you learn about the lifestyle of the former cave residents, such as the “open door” attitude that extended a welcome to all. Courtyards and a maze of alleyways lead from the cathedral, from where you can enjoy a beautiful view of the Sasso Barisano. This is the sassi (literally, “the Stones”) a dense cluster of yellow-white structures that seem to emerge from the earth. Within this starkly beautiful canvas, you walk among typical dwellings, soaring cathedrals, and cavernous edifices. It’s easy to see how it became a stand-in for ancient Jerusalem in the film The Passion of the Christ.

Continue on foot to your luxury hotel—an albergo diffuso spread out across several cave dwellings carved into the tuff rock. Settle in and refresh before reuniting with your guides and travel companions for a welcome aperitivo, taking in the sassi’s incomparable architectural profile. Then savor a special seasonal dinner and a glass or two of the native primitivo wine.

Included Meals: Lunch, Dinner

3 miles, easy to moderate, 570-ft. elevation gain and 795-ft. elevation loss

Awaken to a generous breakfast of cheeses and other local delicacies, an assortment of yogurts, cereals, juices, fresh-baked loaves of bread and pastries, fruit, and, of course, cappuccino!

After a brief walk through the maze of alleyways of Matera, you arrive in the town center where you begin a scenic drive to the Dolomiti Lucane—the southern Dolomites. Amidst this otherworldly setting, you stop first in Castelmezzano. Listed as one of Italy’s most beautiful hamlets, it enjoys a dramatic setting, wedged in a cradle-like basin at the foot of soaring, needle-like massifs. Here, you trace an easygoing circuit around this typical medieval village. Magnificent mountain views accompany you throughout this unforgettable walk.

Make your way to the panoramic terrace of our friend and accomplished chef/restaurateur Antonietta. Antonietta embraces fresh, regional ingredients and the local wild harvest of herbs in her preparations, all inspired by her two muses: her mother and her grandmother. Depending on what’s fresh, you might savor homemade cavatelli pasta with crispy-fried peppers (peperoni cruschi) or local cardoncelli mushrooms. No matter what’s in season, your lunch will be a meal to remember—regional dishes served alfresco and accompanied by grandiose mountain views and perhaps a glass of delicious ficotto, or fig wine.

This afternoon, you return to Matera with time to relax at your hotel or visit some of the many cultural attractions. Afterward, enjoy an evening of independent exploring and dining with recommendations from your guides.

Included Meals: Breakfast, Lunch

4 miles, easy

Today you leave the cultural richness of Matera behind and travel to the lush Valle d’Itria in central Puglia. Blanketed with vineyards and olive groves, the valley is dotted with hundreds of trulli, curious stone structures used by Apulian farmers of centuries past. The buildings feature circular, whitewashed walls and cone-shaped roofs; they were originally constructed without mortar so as to make the structures temporary (an ancient tax loophole!). These “beehives” compel close examination—notably, look for the Paleo-Christian good-luck symbols painted on the roofs.

You reach your trailhead near the 11th-century church of Santa Maria di Barsento, a neighboring town of Alberobello. A picturesque walk leads through green pastures, woodland, and along country lanes flanked by stone walls and seemingly endless olive groves and trulli. Soon, you arrive in the village of Alberobello, a UNESCO World Heritage site whose streets are literally packed with trulli. One of these historic beehive buildings has been transformed into an inviting enoteca; you stop by to meet Gino, who offers a wine tasting along with a light lunch of traditional Apulian snacks.

Following lunch, there is time for you to explore this fairy-tale town on your own; your guides will orient you to the town’s layout. Perhaps head to Piazza del Popolo, or People’s Square, to seek out the town’s hand-woven linens, filet lace, and ceramics at the charming artisanal boutiques. You might also visit the church of St. Anthony, which shares the trulli architectural aesthetic. Or, pop into Pasticceria Martinucci for a delicious gelato.

After, you journey to the “white city” of Ostuni, so nicknamed for its whitewashed buildings. After settling into your hotel, step out with your guides for a special experience and an introduction to this hilltop town overlooking the Adriatic.  Admire its largest buildings including the dramatic 15th-century Ostuni Cathedral and the Bishop’s Palace. Other palazzi stand as legacies to an array of aristocratic families that have made their mark on the town. Afterward, pause for an aperitivo or to shop for some locally crafted ceramics as mementos. For dinner on your own, perhaps dine at one of their favorite osterias along the route. Alternatively, enjoy a relaxing late afternoon at the hotel’s spa, followed by dinner at the hotel’s outstanding bistrot.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take some time to linger over a leisurely breakfast. Bidding farewell to Ostuni, you travel south toward the medieval port of Otranto, your home for the next three nights. En route, stop at an estate near Uggiano la Chiesa in a peaceful oasis blanketed by olive groves and Mediterranean macchia, or scrub. Visit the award-winning passion project of sisters Giulia and Lucia Starace. Here, a team of dedicated weavers works to keep textile arts alive in the 21st century by educating local children about traditional crafts and responsible culture. On arrival, you walk past bushes of myrtle, holm oaks, wild orchids, and one of the oldest beehives in the region. Enjoy a demonstration at the weaving cooperative, recently tapped to contribute to the cruise collection of Parisian fashion house Dior. After, delight in a delicious lunch on the grounds of this special property.

Depart on foot for an easy afternoon walk into the Bronze Age. Your destination is Italy’s megalithic garden in and around neighboring Giurdignano. Home to more than 25 standing-stone menhirs and dolmen, the site provides remarkable insight into an often-forgotten past. Continue your exploration with a visit to an underground olive mill, built in the 16th century, and the 8th-century crypt of San Salvatore, adorned with remarkably preserved 13th-century frescoes.

Your walk culminates at a beautiful whitewashed masseria just outside Otranto, and your home for the next three nights. Enjoy an aperitivo upon arrival, accompanied by typical Salentino snacks. Dinner is on your own this evening; a shuttle is provided into town or you may opt to dine in the masseria’s wonderful restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you travel to Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a scenic location on the Strait of Otranto, which connects the Adriatic and Ionian seas. Greeks, Romans, Byzantines, Normans, and Aragonese have all called this port their own and left their marks on this remarkable city.

This morning’s walking route follows the rocky shores of the Adriatic past rugged coves and caves. Along these coastal cliffs, your progress is marked by the region’s aromatic Mediterranean macchia shrubs and ancient watchtowers—evidence of the defenses erected against Turkish invasions. The stark rocky landscape along the sparkling sea delivers you to a fascinating abandoned bauxite quarry. The stone mined here was once ferried as far away as Venice for the construction of that once-great republic. Today, the quarry resembles a lake in a basin of deep-red walls—hence its local name, Red Lake.

You continue your walk towards the whitewashed Punta Palascia lighthouse, arriving at a family-run agriturismo, where you are welcomed in for a cheesemaking demonstration by a local producer and a light lunch featuring local products—savor antipasti salentini including typical cheeses and homemade bread.

After, continue on foot or by minibus to Porto Badisco, a charming bay whose clear turquoise waters and white-sand floor invite you for a swim. Virgil famously claimed that this sheltered beach was the site of Aeneas’s first landing after he escaped from Troy.

Once you return to the masseria, there’ll be time to relax poolside or treat yourself to a massage before dinner at a nearby winery. This is a truly local experience, and sure to be a highlight of your adventure. After a stroll through the vineyards, with a welcome glass of wine in hand, sit down for a meal that emphasizes the regional specialties. It’s all complemented by a selection of their wines, perhaps a rosé made of the local negroamaro as well as the deep-red native primitivo.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and optional 3 miles, easy

On today’s walk, you trace routes of historical and environmental importance through the Regional Natural Coastal Park of Costa Otranto Santa Maria di Leuca Bosco di Tricase. After breakfast, journey to Marina di Novaglie for the start of your uniquely rewarding day. As you begin, you follow a rocky coastal trail along the sea, passing the typical Salento pajare along the way. These dry-stone structures, like the trulli of Alberobello, might have had their origins as temporary shelters, agricultural storehouses, or dwellings for farm workers.

Your morning destination is Ponte Ciolo, or Ciolo’s Bridge. The town may have been named for the Salentino dialect ciole, or magpies, which are ubiquitous in the region. Several botanical rarities—from Mediterranean onion species to ferns, flowers, and several types of orchids—call this scenic place home, too. Ponte Ciolo gracefully straddles a narrow coastal inlet that has carved out numerous sea caves. Fossils, including those of rhinoceros, and ceramics dating to the Neolithic and the Paleolithic periods, have been found in these remarkable grottoes. Time permitting, you have the option to venture down into the Grotta delle Cipolliane. Though the excursion is not for everyone—it requires negotiating rocks and numerous steps—your effort will be rewarded by being able to dip your toes in the sea. During your time in this scenic enclave, enjoy a break to relax and swim if you wish. There’ll be time for a coffee or drink before continuing on to Santa Maria di Leuca by minibus.

Santa Maria di Leuca is the spot where the Adriatic and Ionian seas swirl together as well as the southernmost point of the Via Francigena. This ancient pilgrim’s route (it translates into “the road from France”) stretches from Canterbury, England to Rome, then continues to Puglia, where pilgrims once continued to the Holy Land by boat. Centuries of other visitors—including traders, pirates, and invaders—have also shaped the history and culture of Capo di Leuca. Upon arrival, you can visit an important religious sanctuary above the town’s harbor—the Basilica de Finibus Terrae, which translates to “basilica at the end of the earth,” an apt term for this seaside outpost at the end of the empire. Your guides will also offer an optional walk along the seaside promenade, pointing out restaurants for lunch on your own. Afterward, return to your masseria, where there’ll be time to relax before the evening meal.

For your final dinner together, you are welcomed at the hotel’s alfresco restaurant with a glass of sparkling prosecco. Settle in for a memorable meal that features the seasonal bounty of the region. You may savor a creamy troccoli: pasta with cuttlefish and black chickpea cream, or risotto with violet shrimp of Gallipoli, pistachios, and pesto, paired with a glass or two of local vino! It’s the ideal way to toast your discovery of the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you stop in the port of Otranto for an hour-long walking tour with your guide. This stunning coastal city boasts a spectacular waterfront and a fascinating medieval past. The city’s highlight is Otranto Cathedral’s enormous, 8,611-square-foot floor mosaic representing the Tree of Life, created by a monk in 1163. Afterward, enjoy free time to explore local craft studios selling clay whistles, baskets, hand-dyed fabric, and ceramics.

Lastly, you will journey to Lecce, the “Florence of the South,” where your tour concludes. Bid farewell to your Country Walkers guides at the Patria Palace Hotel by 12:30 p.m.

Included Meals: Breakfast